Dating Disaster!

This post is going to have a somewhat different twist. Rather than tackling a specific dilemma, question, or topic I am going to sit you down for story time (a story which happened a long time ago). In defiance of the ‘don’t ask don’t tell’ rule of authenticity I am going to openly admit that this story is true – word for word. I have prefaced the story in this way because it is so unbelievable you would definitely think I was lying or exaggerating. Unfortunately, (or perhaps fortunately for the sake of this blog) this actually happened to me exactly as I describe. Sit back, and enjoy the ride:


I had met him at a bar and we had bonded over our mutual distaste for “the bar scene.” We had a fun time chatting over drinks while our friends socialized out on the dance floor. Through my beer haze he seemed cute and nice enough, so I gave him my number. He wasn’t an asshole and a few days later he called and set up a date.

If anything, I was the asshole in this situation. Before the date had even begun I had already decided it wasn’t going anywhere. Knowing this, I probably should have simply canceled. But a few weeks earlier I had been bombarded with “You’re an evil crazy bitch” text messages from a date I’d canceled on; I didn’t want to go down that road again. Instead, I decided to suck it up and stick it out for a quick coffee date.

The plan was that he’d pick me up at 7:30pm and we’d head downtown for coffee. At seven thirty on the dot he showed up on my doorstep, and although he looked just as cute as he had with my beer goggles there simply wasn’t a spark. As I greeted him warmly I thought to myself, ‘I’ll be home in an hour’.

I got in the car and we drove away – actually, we sort of lurched away as he stomped clumsily at the gas pedal. After about the fifth lurched I turned to him and asked if everything was okay. His response was, “Yah, I’m just not a very good driver.” Ugh, shudder. If the date hadn’t been doomed to begin with this would have been its demise. He followed that comment with another, equally unimpressive, comment, “The gas gage isn’t working and I think it’s almost out of gas, so we might have to get out and push.” Ugh, shudder. I wanted to laugh to ease the tension, but I knew he was serious. I took a deep breath, smiled, and thought to myself “I’ll be home in 52 minutes”.

After the initial car fiasco I started asking him some basic questions about his life, school, and work. His answers came out reluctantly, and as I calculated the math in my head I realized why. He clearly knew I had caught on and he blurted out, “Yah, I kind of lied about my age… I thought you were a lot older.” Ugh, shudder. After admitting his true age (2 years younger than he’d initially stated and 1 year younger than me), I suddenly felt like we were decades apart. Still, he was clearly nervous and at least he had confessed the truth. I decided to give him the benefit of the doubt and ride out the rest of the date.

We made it downtown, but it took nearly half an hour for him to find a space that he was comfortable parking in. He finally found one, parked and had taken three steps away from the car before deciding the place was too unsafe. He got back in the car, and with my jaw on the ground, so did I. It took him another 15 minutes to find another parking space. Making idle chat was growing increasingly difficult. Upon the second parking attempt, it didn’t even surprise me when five steps away from the car he looked back saying, “Oh shit!”


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‘Oh shit’ I thought to myself, assuming he’d decided this too was not a safe spot. In frustration clothed in kindness I said, “Don’t worry, this is a safe part of town.” However, It didn’t matter: he was walking back to the car. I decided I’d had enough and didn’t follow him. I stood their annoyed, waiting, and watching him as he stood by his car – just staring at it. Suddenly he turned to me with sullen eyes and said, “I locked my keys in the car!” I wasn’t sure if I wanted to laugh or cry, but it was clear that he wanted to do the latter.

He went into full panic mode, and despite wanting to leave and let him deal with his own problem, I felt bad and stayed. After fifteen minutes of calling various people from his parents to his friends he made arrangements to get keys from someone coming into town. At this point it was nearly 8:30pm. My dreams of being home within the hour had been as far fetched as the possibility of a second date. When he told me that his friend wouldn’t be getting into town until 10:00 I felt my heart sink. At this point, I couldn’t leave the poor guy, but I wasn’t sure if my sanity could maintain another hour and a half.

Despite having already spent an hour together we hadn’t actually gotten that cup of coffee, so we headed into a restaurant and grabbed a seat. Making conversation with this guy was rather painful, and I found myself devouring coffee like it was free tequila. I had to use the sipping motion to hide the look of horror that was plastered on my face after almost every remark he made. I won’t go into specifics, but let’s just say this guy did not lead a very exciting or grown up life. At one point he even admitted, ‘I feel like you’re a lot more mature than me.’ Ugh, shudder – Yah, clearly buddy, but pointing that out just makes it more awkward!

Six cups of coffee later and ten minutes to ten, we left. My head was buzzing from the caffeine, and I hoped it would give me enough energy to make idle chatter through the drive home. We walked to the spot where his friend was supposed to meet us and talked about something mundane: the weather. At 10:10 my blood was starting to boil a bit – or perhaps that was just the last cup of coffee kicking in. At 10:15 there was still no sign of the friend. At 10:20 my date’s cell phone buzzed and hummed: it was a text from the friend, “late b there soon.” Ugh, mother-fucking shudder!!!

We decided to walk around a bit – mostly because making eye contact was becoming somewhat agonizing. I desperately wanted to leave, but he was so obviously embarrassed that I just couldn’t bring myself to do it. Clearly, karma was kicking my ass for not canceling the date in the first place. At 10:50, when I should have been safe and warm in the abode of my apartment, his friend finally responded to the ‘GET THE FUCK OVER HERE’ text that had been sent earlier. After reading the response, my mortified date looked at me with those same sullen eyes, “He went to a party."

“He went to a party?” I asked, confused.

Emotionless, “He went to a party.”

With rage, “He went to a PARTY?”

With defeat, “He went to a party!”

Angry texts were sent. Apparently calls couldn’t be made because it was long distance (At this point I didn’t even care that that fact contradicted some of his other story lines.) Zero responses came. Was this really happening?
My date suggested we go to a COFFEE shop to kill some more time. Seriously, more coffee? I was hoping for a lobotomy. Nonetheless, we hit up the first coffee shop we could find, and my body convulsed in a painful yet delightful way as more caffeine was poured into my veins. We were forced onto the streets, again, after the coffee shop closed, and at this point he finally uttered the first satisfying words of the night, “You don’t have to stay. Why don’t you take the bus home.” I wanted to take him up on the offer. I really did. Unfortunately, in line with karma, my last bus drove by just as he said those words. Fuck. Sigh. Ah well… At this point it was kind of like waiting in line at emergency; it had already been hours so you might as well wait it out and see what the diagnosis is. (I had a feeling it wasn’t going to be pretty.)

This is where the story really gets awkward. We went for another walk – not exactly the kind of exercise you hope to get on a date – and ended up by some beautiful historic buildings. Suddenly, I began to panic. I realized what was happening as my brain went back to a conversation I’d had earlier that week. A male friend had explained to me his perfect first date strategy which ended with a quaint stroll around the historic buildings and a kiss at a lookout point. Holy shit! It couldn’t be? He wasn’t? There was no way!

I saw the lookout ahead. I suggested we turn back. He suggested we go to the lookout. My heart was racing, but I was hoping it was just a coincidence. We got to the lookout. I strategically placed myself in a position that would make it awkward for him to try anything. He would look like a fool if he went in for the kill. And then… OH MY GOD! Yup, he tried to kiss me.

Let me emphasize that the key word there is tried. My pity for him was up. I let him know that a kiss was not happening, and quickly marched off in the opposite direction. We got to a bench and sat for a long time: mostly in silence. The rest of the date – if it could even be called that anymore – involved almost no talking. At 11:50 his friend finally texted and met us at the car. The friend was highly intoxicated, loud, and incredibly annoying. He made a few ignorant comments like, “Did you guys do it?” before passing out in the back seat. No words were exchanged on the ride home until we pulled into my driveway. He stopped the car, awkwardly cleared his throat and questioned, “Should I get out and walk you to the door?” I thanked him and said no, but perhaps slammed the door a bit harshly.

A few minutes later I was curled up under the covers thankful that I had survived one of the worst dates imaginable. At that moment, I swore to myself I’d never go on a casual date again unless I honestly thought the guy was worth more than an hour of my time

… let’s just say I haven’t been on many dates since.

Now, it’s your turn and spare no detail!